TW202000875A - Method for extracting sesame lignans from by-product generated from production of sesame oil capable of extracting sesame lignans from a by-product containing a relatively low amount, such as 1.5 weight%, of sesame lignans - Google Patents
Method for extracting sesame lignans from by-product generated from production of sesame oil capable of extracting sesame lignans from a by-product containing a relatively low amount, such as 1.5 weight%, of sesame lignans Download PDFInfo
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- 241000207961 Sesamum Species 0.000 title claims abstract description 78
- 235000003434 Sesamum indicum Nutrition 0.000 title claims abstract description 78
- 150000005692 lignans Chemical class 0.000 title claims abstract description 72
- 229930013686 lignan Natural products 0.000 title claims abstract description 71
- 235000009408 lignans Nutrition 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 36
- 239000008159 sesame oil Substances 0.000 title claims abstract description 18
- 235000011803 sesame oil Nutrition 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000006227 byproduct Substances 0.000 title abstract description 17
- 238000000199 molecular distillation Methods 0.000 claims abstract description 59
- 238000005886 esterification reaction Methods 0.000 claims abstract description 25
- 230000032050 esterification Effects 0.000 claims abstract description 22
- 230000004048 modification Effects 0.000 claims abstract description 3
- 238000012986 modification Methods 0.000 claims abstract description 3
- 239000003921 oil Substances 0.000 claims description 14
- 235000019198 oils Nutrition 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 14
- 235000021588 free fatty acids Nutrition 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- PEYUIKBAABKQKQ-AFHBHXEDSA-N (+)-sesamin Chemical compound C1=C2OCOC2=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-AFHBHXEDSA-N 0.000 claims description 7
- PEYUIKBAABKQKQ-UHFFFAOYSA-N epiasarinin Natural products C1=C2OCOC2=CC(C2OCC3C2COC3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- VRMHCMWQHAXTOR-CMOCDZPBSA-N sesamin Natural products C1=C2OCOC2=CC([C@@H]2OC[C@@]3(C)[C@H](C=4C=C5OCOC5=CC=4)OC[C@]32C)=C1 VRMHCMWQHAXTOR-CMOCDZPBSA-N 0.000 claims description 5
- 239000010779 crude oil Substances 0.000 claims description 3
- 239000008130 destillate Substances 0.000 claims description 3
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 claims description 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 9
- 238000002425 crystallisation Methods 0.000 abstract description 5
- 230000008025 crystallization Effects 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 9
- 238000011084 recovery Methods 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000007407 health benefit Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
本發明係有關一種由生產芝麻油過程中所產生的副產物中提取芝麻木酚素的方法，尤其有關一種由芝麻木酚素含量很低，例如約1.5重量%，的副產物中提取芝麻木酚素的方法。The invention relates to a method for extracting sesame lignan from the by-products produced in the process of producing sesame oil, in particular to a method for extracting sesame lignan from the by-products with a low content of sesame lignan, for example, about 1.5% by weight Vegetarian method.
自芝麻中提取芝麻木酚素已有一段時間的技術發展，提取的原料有芝麻籽、芝麻油、芝麻餅粕、生產芝麻油所產生的各類副產物等；提取方法有傳統的溶劑萃取、管柱層析、超臨界、蒸餾法或分子蒸餾等。其中溶劑萃取為利用甲醇、乙醇、乙醚等從芝麻油中直接提取芝麻木酚素，然後再進行常溫或低溫結晶純化，成本低但操作時間、溶劑回收率、工作量均較大，且可能有溶劑殘留風險。The technology of extracting sesame lignan from sesame has been developed for a period of time. The raw materials extracted include sesame seeds, sesame oil, sesame cake meal, various by-products produced from the production of sesame oil, etc.; the extraction methods include traditional solvent extraction and column Chromatography, supercritical, distillation or molecular distillation, etc. Among them, solvent extraction is to directly extract sesame lignan from sesame oil using methanol, ethanol, ether, etc., and then perform crystallization purification at normal temperature or low temperature. The cost is low but the operation time, solvent recovery rate, workload are large, and there may be a solvent Residual risk.
管柱層析法之產量極低，成本高，且會耗用大量溶劑，不適合工業化生產；超臨界流體雖然不需用溶劑，但生產與設備成本是幾種方法之最。The output of column chromatography is extremely low, the cost is high, and it will consume a lot of solvents, which is not suitable for industrial production. Although supercritical fluids do not require solvents, the cost of production and equipment is the most of several methods.
以分餾法或分子蒸餾法能改善先前技術缺憾，增加大量生產的效率，如、US5209826號、CN103896955號與CN104292238號專利文件所揭示，利用分子蒸餾提取芝麻油中芝麻木酚素，再以結晶法純化，可得高純度芝麻木酚素，且不需其他方法輔助；蒸餾或分子蒸餾設備已廣泛於魚油、維他命提取生產等，有產業利用性高、穩定性高、溫度低、耗能小，產量適中的優勢。Fractional distillation or molecular distillation can improve the shortcomings of the prior art and increase the efficiency of mass production. As disclosed in US Patent Nos. 5,209,826, CN103896955 and CN104292238, molecular distillation is used to extract sesame lignan in sesame oil, and then purified by crystallization , High-purity sesame lignan can be obtained without the assistance of other methods; distillation or molecular distillation equipment has been widely used in fish oil, vitamin extraction production, etc., has high industrial utilization, high stability, low temperature, low energy consumption, and output Moderate advantage.
另一方面，提取芝麻木酚素的方法受到提取原料本身特性限制大，對於使用之原料仍有一定程度限制，如CN103896955號文件僅利用分子蒸餾為一段提取，因此僅能作用於品質較高、雜質較低的食用芝麻油，原料成本相對高、壓縮食用油的總量，且提取過芝麻木酚素的芝麻油，因主要健康功效成分已被取出，能否作為一般食用芝麻油販賣或使用將受到許多挑戰。On the other hand, the method of extracting sesame lignan is greatly restricted by the characteristics of the extracted raw materials, and the raw materials used are still limited to a certain extent. For example, the document CN103896955 only uses molecular distillation to extract for a period, so it can only act on high quality, The edible sesame oil with low impurities has relatively high raw material costs, compresses the total amount of edible oil, and sesame oil with sesame lignan extracted has been taken out because of its main health benefits. Whether it can be sold or used as general edible sesame oil will be subject to many challenge.
而CN104292238號文件使用榨完油後之芝麻餅粕，以溶劑取出油再進行提取，雖然可說是製程副產物的利用，對原料成本與利用率皆有幫助，卻因副產物雜質、游離脂肪酸較多，而必須以冷凍乾燥、溶劑提取等做預處理，失去了蒸餾或分子蒸餾的優勢。Document No. CN104292238 uses sesame cake meal after oil extraction, and extracts the oil with a solvent to extract it. Although it can be said that the use of by-products in the process is helpful to the cost and utilization of raw materials, it is due to by-product impurities and free fatty acids. Many, but must be pre-treated by freeze-drying, solvent extraction, etc., lost the advantages of distillation or molecular distillation.
US5209826雖然使用芝麻油之脫臭脫餾物作為原料提取其中芝麻木酚素，但該脫臭脫餾物仍含有約31%芝麻木酚素，並非針對低芝麻木酚素含量的副產物進行提取，且US5209826使用降膜式(falling film)分子蒸餾設備，其效率不高，目前在工業生產上已較少使用。US5209826 Although the deodorized dewaxate of sesame oil is used as a raw material to extract sesame lignan, the deodorized destillate still contains about 31% sesame lignan, which is not for the extraction of by-products with low sesame lignan content. Moreover, US5209826 uses falling film molecular distillation equipment, which has low efficiency and is currently less used in industrial production.
本發明的一主要目的在提供一種由生產芝麻油過程中所產生的副產物中提取芝麻木酚素的方法，其中該副產物的芝麻木酚素含量低雜質高，尤以游離脂肪酸為主，導致分離不易或得率不佳，芝麻木酚素含量甚至僅約1.5重量%或更低。A main object of the present invention is to provide a method for extracting sesame lignan from by-products produced in the process of producing sesame oil, wherein the by-product sesame lignan content is low in impurities and high in impurities, especially free fatty acids, which leads to The separation is not easy or the yield is poor, and the content of sesame lignan is only about 1.5% by weight or less.
為了達成上述本發明目的，一種依照本發明內容所完成的芝麻木酚素提取方法包含幾個特點：將該副產物進行酯化反應；將所得到的酯化反應產物混合物於140℃~200℃的溫度及真空度1×10-3 ~ 10×10-3 mbar的壓力進行第一階段分子蒸餾，獲得一含芝麻木酚素和一游離脂肪酸之餾出物；及將所得到的餾出物於90℃~120℃的溫度及真空度1×10-3 ~ 10×10-3 mbar的壓力進行第二階段分子蒸餾，獲得一含芝麻木酚素的餾餘物，該餾餘物的芝麻木酚素含量可高至30重量%以上。該餾餘物可以進一步被純化，例如結晶處理，以得到可得更高純度之芝麻木酚素產品，例如純度大於80%的芝麻木酚素產品。In order to achieve the above object of the present invention, a method for extracting sesame lignans according to the present invention includes several features: performing esterification reaction on the by-product; and obtaining the obtained esterification reaction product mixture at 140°C to 200°C The temperature and vacuum degree of 1×10 -3 ~ 10×10 -3 mbar were used for the first stage molecular distillation to obtain a distillate containing sesame lignan and a free fatty acid; and the resulting distillate The second stage molecular distillation is carried out at a temperature of 90° C. to 120° C. and a vacuum degree of 1×10 −3 to 10×10 −3 mbar to obtain a residuum containing sesame lignan, and the sesame of the residuum The lignan content can be as high as 30% by weight or more. The distillate can be further purified, such as crystallization treatment, to obtain sesame lignan products with higher purity, such as sesame lignan products with a purity greater than 80%.
前述的第一階段分子蒸餾有助於餾出芝麻木酚素與脂肪酸酯，使之與各式雜質分離；該酯化反應及第二階段分子蒸餾，能將脂肪酸酯與芝麻木酚素分離，減少芝麻木酚素被該第二階段分子蒸餾的餾出物所攜帶流失。The aforementioned first-stage molecular distillation helps to distill sesame lignans and fatty acid esters to separate them from various impurities; the esterification reaction and the second stage molecular distillation can separate fatty acid esters and sesame lignans Separation reduces the loss of sesame lignans carried by the distillate of the second stage molecular distillation.
本發明以芝麻油榨取、精煉製程中自然產生的油類副產物為芝麻木酚素提取原料，一方面確保芝麻整體利用性，二方面將此類原作為廢棄物的副產物拿來提煉脂溶性芝麻木酚素，可降低整體生產成本，其中壓榨過濾產生的過濾油腳、沉降油腳，精煉餅粕產生的浸出毛油、脫酸帶出油料及脫臭脫餾物皆為生產過程中自然產生油相，因此不用溶劑浸提即可得油脂混合物。In the present invention, the oil by-products naturally produced in the process of sesame oil extraction and refining are sesame lignan extract raw materials, on the one hand, the overall availability of sesame is ensured, and on the other hand, such raw waste products are used as waste by-products to extract fat-soluble sesame Lignin can reduce the overall production cost. Among them, the filter oil foot and sedimentation oil foot generated by squeezing and filtering, the leached crude oil produced by the refined cake, the oil produced by the deacidification and the deodorized deaerator are all naturally produced in the production process. The oil phase, therefore, the oil mixture can be obtained without solvent extraction.
惟此類副產物雜質較高，尤以游離脂肪酸為主，因此在本發明中先進行酯化前處理，使酯化後游離脂肪酸的沸點與芝麻木酚素拉開較大差異，便可在分餾或分子蒸餾中將其移除，省下其他方法處理的工與時間，達到副產物利用、省能、省時的目的。However, the impurities in such by-products are relatively high, especially free fatty acids. Therefore, in the present invention, pre-esterification treatment is carried out first, so that the boiling point of free fatty acids after esterification is greatly different from that of sesame lignan. It is removed in fractional distillation or molecular distillation, saving the time and labor of other methods to achieve the purpose of by-product utilization, energy saving and time saving.
依本發明的一較佳具體實施例所完成的一種由芝麻木酚素原料中提取芝麻木酚素的方法包括下列步驟: (1) 將該芝麻木酚素原料進行酯化改質； (2) 進行一第一階段分子蒸餾，其操作溫度介於140℃~200℃，較佳的160℃~170℃，獲得一含芝麻木酚素和一游離脂肪酸之餾出物； (3) 針對上述該餾出物進行第二階段分子蒸餾，其操作溫度介於90℃~120℃，較佳的90℃~100℃，獲得一含芝麻木酚素之餾餘物； (4) 由該餾餘物取得該芝麻木酚素。According to a preferred embodiment of the present invention, a method for extracting sesame lignan from sesame lignan raw material includes the following steps: (1) esterification modification of the sesame lignan raw material; (2 ) Perform a first stage molecular distillation with an operating temperature between 140°C and 200°C, preferably 160°C and 170°C, to obtain a distillate containing sesame lignan and a free fatty acid; (3) For the above The distillate is subjected to a second-stage molecular distillation, and its operating temperature is between 90°C and 120°C, preferably 90°C and 100°C, to obtain a distillate containing sesame lignan; (4) from the distillate The sesame lignan.
上述本發明方法中的第一階段分子蒸餾及第二階段分子蒸餾，較佳的係在真空度1×10-3 ~ 10×10-3 mbar的壓力下進行；更佳的，係使用刮膜式(wiped-film)分子蒸餾設備進行。The above-mentioned first-stage molecular distillation and second-stage molecular distillation in the method of the present invention are preferably carried out under a vacuum of 1×10 −3 to 10×10 −3 mbar; more preferably, a scraped film is used (Wiped-film) molecular distillation equipment.
適合作為上述本發明方法中的芝麻木酚素原料包括（但不限於）芝麻油生產過程中產出之過濾油腳、沉降油腳、浸出毛油、脫酸帶出油料或脫臭脫餾物，較佳的係脫臭脫餾物。Suitable as sesame lignan raw materials in the above method of the present invention include (but are not limited to) filter oil feet, sediment oil feet, leaching crude oil, deacidification to bring out oil or deodorized deaerators produced in the production process of sesame oil, The preferred system is deodorized deaerator.
上述本發明方法中的芝麻木酚素包括（但不限於）芝麻素、表芝麻素、芝麻林素或芝麻酚。The sesamin in the above method of the present invention includes (but is not limited to) sesamin, episesamin, sesamin, or sesamol.
上述本發明方法的第(1)步驟中的酯化係指甲基酯化或乙基酯化。The above-mentioned esterification in the step (1) of the method of the present invention refers to methyl esterification or ethyl esterification.
上述本發明方法的第(4)步驟較佳的包括使用醇類溶劑對該餾餘物進行結晶處理。 實施例：The above step (4) of the method of the present invention preferably includes crystallizing the distillate with an alcoholic solvent. Example:
以下實施例所用之脫餾物為芝麻油(壓榨或浸出方式生產)進行食用油脂精煉脫臭製程所得之脫餾產物。脫餾物的甲基酯化及乙基酯化方式均為酸催化，它們的反應條件為：The de-distillate used in the following examples is the de-distillation product obtained from the sesame oil (produced by pressing or leaching) through the process of refining and deodorizing edible oils and fats. The methyl esterification and ethyl esterification of the distillate are both acid catalyzed, and their reaction conditions are:
甲基酯化步驟：150克之芝麻油脫餾物與1500毫升甲醇及0.46 mL硫酸混和，於80℃反應2小時，減壓濃縮去除甲醇後進行水洗，再減壓濃縮去除水分，以濾紙過濾甲酯化脫餾物中無法溶解之雜質，甲酯化產物重量約為144克。Methyl esterification step: 150 grams of sesame oil distillate is mixed with 1500 ml of methanol and 0.46 ml of sulfuric acid, and reacted at 80° C. for 2 hours, concentrated under reduced pressure to remove methanol, washed with water, then concentrated under reduced pressure to remove water, and filtered methyl ester with filter paper The insoluble impurities in the chemical degassed product weigh approximately 144 grams of methylated product.
乙基酯化步驟：200克之芝麻油脫餾物與2000毫升無水乙醇及0.64 mL濃硫酸混和，於80℃反應4小時，減壓濃縮去除乙醇後進行水洗，再減壓濃縮去除水分，以濾紙過濾乙酯化脫餾物中無法溶解之雜質，乙酯化產物約為204克。 實施例一：Ethyl esterification step: 200 grams of sesame oil distillate was mixed with 2000 ml of absolute ethanol and 0.64 mL of concentrated sulfuric acid, and reacted at 80° C. for 4 hours. The ethanol was concentrated under reduced pressure and washed with water, then concentrated under reduced pressure to remove water, and filtered with filter paper Impurities that cannot be dissolved in the ethylate destillate, the ethylate product is about 204 grams. Example one:
將脫餾物進行上述甲基酯化步驟後，進行兩段分子蒸餾，第一段以140℃餾出大部分芝麻木酚素及脂肪酸甲酯提高收率，第二段再以100℃餾出脂肪酸甲酯，詳細步驟如下：After the distillate is subjected to the above-mentioned methyl esterification step, two-stage molecular distillation is carried out. The first stage distills most sesame lignans and fatty acid methyl esters at 140°C to increase the yield, and the second stage distills at 100°C Fatty acid methyl ester, detailed steps are as follows:
1. 將脫餾物進行上述的酸催化甲基酯化步驟，使其中的游離脂肪酸生成脂肪酸甲酯。1. The distillate is subjected to the above-mentioned acid-catalyzed methyl esterification step to generate fatty acid methyl esters of free fatty acids therein.
2. 利用刮膜式分子蒸餾設備進行分子蒸餾，條件為冷凝溫度60℃、真空度約6×10-3 mbar，脫餾物酯化產物的進料流速2-3 mL/min，刮板轉速100 rpm，以140℃餾出芝麻木酚素及脂肪酸甲酯。計算此餾出物的芝麻木酚素濃度及重量，以甲酯化後之脫餾物而言，此分子蒸餾製程之餾出物的芝麻木酚素回收率為60.8重量%。2. Perform molecular distillation using a wiped film molecular distillation equipment under the conditions of a condensation temperature of 60°C, a vacuum of about 6×10 -3 mbar, a feed flow rate of the esterified product of the distillate of 2-3 mL/min, and a scraper speed At 100 rpm, sesame lignan and fatty acid methyl ester were distilled off at 140°C. Calculate the sesame lignan concentration and weight of this distillate. In terms of the distillate after methylation, the sesame lignan recovery of this molecular distillation process distillate is 60.8% by weight.
3. 利用刮膜式分子蒸餾設備進行分子蒸餾，條件為冷凝溫度60℃、真空度約6×10-3 mbar，餾出物的進料流速2-3 mL/min，刮板轉速100 rpm，以100℃餾出脂肪酸甲酯。餾出物未檢出芝麻木酚素；以140℃分子蒸餾餾出物而言，100℃分子蒸餾餾餘物中芝麻木酚素回收率為76.5重量%。 實施例二：3. Perform molecular distillation using a wiped film type molecular distillation equipment under the conditions of a condensing temperature of 60°C, a vacuum of about 6×10 -3 mbar, a feed flow rate of distillate of 2-3 mL/min, and a scraper speed of 100 rpm. Fatty acid methyl ester was distilled off at 100°C. No sesame lignan was detected in the distillate; in terms of 140°C molecular distillation distillate, the recovery rate of sesame lignan in the molecular distillation distillate at 100°C was 76.5% by weight. Example 2:
將脫餾物進行上述甲基酯化步驟後，進行兩段分子蒸餾，第一段以170℃餾出芝麻木酚素及脂肪酸甲酯提高收率，第二段再以100℃餾出脂肪酸甲酯，餘下的高濃度芝麻木酚素餾餘物利用溶劑結晶法進行晶析純化，取得純度80重量%以上之芝麻木酚素，詳細步驟如下：After the distillate is subjected to the above-mentioned methyl esterification step, two-stage molecular distillation is carried out. The first stage distills sesame lignan and fatty acid methyl ester at 170°C to increase the yield, and the second stage distills fatty acid A at 100°C. Ester, the remaining high-concentration sesame lignan residue is crystallized and purified by solvent crystallization to obtain sesame lignan with a purity of more than 80% by weight. The detailed steps are as follows:
1. 將脫餾物進行酸催化之上述的甲基酯化步驟，使其中的游離脂肪酸生成脂肪酸甲酯。1. The distillate is subjected to the acid-catalyzed methyl esterification step described above to generate fatty acid methyl esters of the free fatty acids therein.
2. 利用刮膜式分子蒸餾設備進行分子蒸餾，條件為冷凝溫度60℃、真空度約6×10-3 mbar，脫餾物酯化產物的進料流速2-3 mL/min，刮板轉速100 rpm，以170℃餾出芝麻木酚素及脂肪酸甲酯。2. Perform molecular distillation using a wiped film molecular distillation equipment under the conditions of a condensation temperature of 60°C, a vacuum of about 6×10 -3 mbar, a feed flow rate of the esterified product of the distillate of 2-3 mL/min, and a scraper speed At 100 rpm, sesame lignan and fatty acid methyl ester were distilled off at 170°C.
計算此餾出物的芝麻木酚素濃度及重量，以甲酯化後之脫餾物而言，此分子蒸餾製程之餾出物的芝麻木酚素回收率為97.28重量%；餾餘物則未檢出。Calculate the concentration and weight of sesame lignan in this distillate. In terms of the distillate after methylation, the recovery rate of sesame lignan in this molecular distillation process is 97.28% by weight; the distillate not detected.
3. 利用刮膜式分子蒸餾設備進行分子蒸餾，條件為冷凝溫度60℃、真空度約6×10-3 mbar，餾出物進料流速2-3 mL/min，刮板轉速100 rpm，以100℃餾出脂肪酸甲酯。餾出物未檢出芝麻木酚素，餾餘物之芝麻木酚素純度提高至38.86重量%；以170℃分子蒸餾餾出物而言，芝麻木酚素回收率回收率為89.66重量%。3. Perform molecular distillation using a wiped film molecular distillation equipment under the conditions of a condensing temperature of 60°C, a vacuum of about 6×10 -3 mbar, a distillate feed flow rate of 2-3 mL/min, and a scraper speed of 100 rpm. Fatty acid methyl ester was distilled off at 100°C. No sesame lignans were detected in the distillate, and the purity of the sesame lignans in the distillate was increased to 38.86% by weight; in terms of 170°C molecular distillation distillate, the sesame lignan recovery rate was 89.66% by weight.
4. 將餾餘物溶於熱乙醇（60℃）後，再進行室溫冷卻（約26℃）使結晶固形物析出。析出物先置於4℃冰箱冷卻，再過濾此部分之固形物(冷藏析出物)後，再將濾液放置於-20℃冰箱冷凍，再將析出之固形物過濾(冷凍析出物)。冷藏析出物其芝麻木酚素純度為85.11重量%，另有7.13重量%之植物固醇；冷凍析出物芝麻木酚素純度則為56.98重量%。若將冷藏與冷凍之固形物合併計算，其芝麻木酚素純度約為82.28重量%，總回收率約為85.99重量%。 實施例三：4. After dissolving the distillate in hot ethanol (60 ℃), then cooling at room temperature (about 26 ℃) to precipitate crystalline solids. The precipitate is first placed in a 4°C refrigerator to cool, then the solids in this part (refrigerated precipitates) are filtered, and then the filtrate is placed in a -20°C refrigerator to freeze, and then the precipitated solids are filtered (frozen precipitates). The refrigerated precipitate had a sesame lignan purity of 85.11% by weight and another 7.13% by weight phytosterol; the frozen precipitate sesame lignan had a purity of 56.98% by weight. If refrigerated and frozen solids are combined, the purity of sesame lignan is about 82.28% by weight, and the total recovery rate is about 85.99% by weight. Example three:
將脫餾物進行上述乙基酯化步驟後，進行兩段分子蒸餾，第一段以160℃餾出大部分芝麻木酚素及脂肪酸乙酯提高收率，第二段再以100℃餾出脂肪酸乙酯，詳細步驟如下：After the distillate is subjected to the above-mentioned ethyl esterification step, two-stage molecular distillation is performed. The first stage distills most sesame lignans and fatty acid ethyl esters at 160°C to increase the yield, and the second stage distills at 100°C Fatty acid ethyl ester, detailed steps are as follows:
1. 將脫餾物進行上述的酸催化乙基酯化步驟，使其中的游離脂肪酸生成脂肪酸乙酯。1. The distillate is subjected to the above-mentioned acid-catalyzed ethyl esterification step to generate fatty acid ethyl esters of free fatty acids therein.
2. 利用刮膜式分子蒸餾設備進行分子蒸餾，條件為冷凝溫度60℃、真空度約1~3×10-3 mbar，脫餾物酯化產物進料流速2-3 mL/min，刮板轉速100 rpm，以160℃餾出芝麻木酚素及脂肪酸乙酯。160℃分子蒸餾餾出物經計算芝麻木酚素濃度及重量後，以乙酯化後之脫餾物而言，此分子蒸餾製程之餾出物其芝麻木酚素回收率為96.96重量%；餾餘物則未檢出。2. Perform molecular distillation using a wiped film molecular distillation equipment under the conditions of a condensing temperature of 60°C, a vacuum of about 1~3×10 -3 mbar, a feed rate of 2-3 mL/min for the esterification product of the distillate, and a scraper At a rotation speed of 100 rpm, sesame lignan and fatty acid ethyl ester were distilled off at 160°C. After calculating the concentration and weight of sesame lignan in 160°C molecular distillation distillate, in terms of the distillate after ethylation, the recovery rate of sesame lignan in this molecular distillation process is 96.96% by weight; No distillate was detected.
3. 利用刮膜式分子蒸餾設備進行分子蒸餾，條件為冷凝溫度60℃、真空度約1~3×10-3 mbar，餾出物的進料流速2-3 mL/min，刮板轉速100 rpm，以100℃餾出脂肪酸乙酯，以160℃分子蒸餾餾出物而言，100℃分子蒸餾餾出物中芝麻木酚素回收率為4.61重量%。餾餘物中芝麻木酚素純度約為40.11重量%；以160℃分子蒸餾餾出物而言，100℃分子蒸餾餾餘物中芝麻木酚素回收率為73.83重量%。3. The molecular distillation using the wiped film type molecular distillation equipment is carried out under the conditions of condensing temperature 60℃, vacuum degree of about 1~3×10 -3 mbar, feed flow rate of distillate 2-3 mL/min, scraper speed 100 At rpm, the fatty acid ethyl ester was distilled off at 100°C and the molecular distillation distillate at 160°C. The recovery rate of sesame lignan in the molecular distillation distillate at 100°C was 4.61% by weight. The purity of sesame lignan in the distillate is about 40.11% by weight; in terms of 160°C molecular distillation distillate, the recovery rate of sesame lignan in 100°C molecular distillation distillate is 73.83% by weight.
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